The present invention relates to a new herbicidal composition.
At the present time, it is known that an N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1) described below has herbicidal activity (See U.S. Pat. No. 4,770,695, U.S. Pat. No. 4,640,707, U.S. Pat. No. 5,062,884 and so on).
In a field of herbicide, requested are how can an application of less amount of herbicide attain same herbicidal effect as an application of usual amount of it.
The present inventor has intensively studied to find out a method for boosting herbicidal activity of the N-phenyltetrahydrophthalimide compound. As a result he has found that, when the N-phenyltetrahydrophthalimide compound was applied with an insecticidal organophosphorus compound, the herbicidal activity of the N-phenyltetrahydrophthalimide compound against weeds was higher than when the N-phenyltetrahydrophthalimide compound was solely applied.
Thus, the present invention provides a herbicidal composition of the N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1): 
wherein R1 represents hydrogen or halogen; R2 represents halogen and R3 represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6 alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R2 and R3 represent together xe2x80x94Oxe2x80x94CHR4xe2x80x94C(xe2x95x90O)xe2x80x94NR5xe2x80x94, whose oxygen connected to 4-position of the benzene ring, whose nitrogen connected to 5-position of the benzene ring, wherein R4 represents hydrogen or methyl and R5 represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy) C1-C3 alkyl,
and an effective amount for increasing herbicidal activity of the N-phenyltetrahydrophthalimide compound of an insecticidal organophosphorus compound (hereinafter, referred to as the present composition); and a method for controlling weeds which comprises of applying said N-phenyltetrahydrophthalimide compound with the insecticidal organophosphorus compound to weeds or to a place where weeds are growing or will grow (hereinafter referred to as the present method).
The N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1) (hereinafter referred to as the present imide compound) includes the compounds described below.
A compound wherein R2 and R3 are together xe2x80x94Oxe2x80x94CHR4xe2x80x94C(xe2x95x90O)xe2x80x94NR5xe2x80x94 in Chemical Formula (1), that is represented by Chemical Formula (4): 
wherein R1, R4 and R5 are as defined above;
a compound wherein R1 is fluorine in Chemical Formula (4);
a compound wherein R4 is hydrogen in Chemical Formula (4);
a compound wherein R5 is C3-C6 alkynyl in Chemical Formula (4);
a compound wherein R1 is fluorine, R4 is hydrogen and R5 is C3-C6 alkynyl in Chemical Formula (4);
a compound wherein R2 is R21 and R3 is R31 in the Chemical Formula (1), that is represented by Chemical Formula (5): 
xe2x80x83wherein R1 are as defined above, R21 represents halogen and R31 represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6 alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl;
a compound wherein R1 is fluorine in Chemical Formula (5);
a compound wherein R21 is chlorine in Chemical Formula (5);
a compound wherein R31 is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy in Chemical Formula (5);
a compound wherein R31 is C1-C6 alkynyloxy in Chemical Formula (5);
a compound wherein R31 is (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl in Chemical Formula (5);
a compound wherein R1 is fluorine, R21 is chlorine and R31 is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy in Chemical Formula (5).
Furthermore, the present imide compound includes the compounds described below.
N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide 
(common name: flumioxazin);
pentyl[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)-4-fluorophenoxy]acetate 
(common name: flumiclorac-pentyl);
(Z)-ethyl 2-chloro-3-[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)phenyl]acrylate 
(common name: cinidon-ethyl);
N-(4-chlorophenyl)cyclohex-1-ene-1,2-dicarboxamide 
(common name: chlorphthalim).
The insecticidal organophosphorus compound in the present invention includes, for example, the compounds described below.
A compound represented by Chemical Fonnula (6): 
wherein X1 represents oxygen or sulfur, X2 represents oxygen, sulfur or direct bond between phosphorous atom and R8, R6 represents lower alkyl, R7 represents lower alkoxy, lower alkylthio, lower alkylcarbonylamino or phenyl, R8 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted phenyl or optionally substituted heteroaryl;
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkylcarbonylamino and R8 is optionally substituted C1-C4 alkyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is sulfur, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted C1-C4 alkyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted alkenyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted phenyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkylthio and R8 is optionally substituted phenyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted pyrimidinyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted pyridyl in the Chemical Formula (6);
a compound wherein X1 is sulfur, X2 is oxygen, R6 is C1-C4 alkyl, R7 is C1-C4 alkoxy and R8 is optionally substituted isoxazolyl in the Chemical Formula (6).
Furthermore, the insecticidal organophosphorus compound includes the compounds described below.
O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate (common name: fenitrothion);
O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate (common name: fenthion);
O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate (common name: diazinon);
O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (common name: chlorpyrifos);
O,S-dimethyl acetylphosphoramidothioate (common name: acephate);
S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioate (common name: methidathion);
O,O-diethyl S-2-ethylthioethyl phosphorodithioate (common name: disulfoton);
2,2-dichlorovinyl dimethyl phosphate (common name: dichlorvos);
O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate (common name: sulprofos);
O-4-cyanophenyl O,O-dimethyl phosphorothioate (common name: cyanophos);
O,O-dimethyl S-methylcarbamoylmethyl phosphorodithioate (common name: dimethoate);
S-xcex1-ethoxycarbamoylbenzyl O,O-dimethyl phosphorodithioate (common name: phenthoate);
diethyl (dimethoxythiophosphorylthio)succinate (common name: malathion);
dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate (common name: trichlorfon);
S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate (common name: azinphos-methyl);
dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate (common name: monocrotophos);
O,O,Oxe2x80x2,Oxe2x80x2-tetraethyl S,Sxe2x80x2-methylene bis(phosphorodithioate) (common name: ethion);
S-2-ethylthioethyl O,O-dimethyl phosphorodithioate (common name: thiometon);
O,O-diethyl O-(5-phenyl-1,2-oxazol-3-yl) phosphorothioate (common name: isoxathion);
O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate (common name: vamidothion);
O-2,4-dichlorophenyl O-ethyl S-propyl phosphorodithioate (common name: prothiofos);
S-2-ethylsulfinyl-1-methylethyl] O,O-dimethyl phosphorothioate (common name: xydeprofos).
The present imide compound can be produced according to the procedures described, for example, in U.S. Pat. No. 4,770,695, U.S. Pat. No. 4,640,707, U.S. Pat. No. 5,062,884 and the others.
The present composition has herbicidal activity in the foliar treatment and the soil treatment on upland field against various weeds such as listed below.
Polygonaceous weeds:
wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), pennsylvania smartweed (Polygonum pensylvanicum), ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)
Portulacaceous weeds:
common purslane (Portulaca oleracea)
Caryophyllaceous weeds:
common chickweed (Stellaria media)
Chenopodiaceous weeds:
common lambsquarters (Chenopodium album), kochia (Kochia scoparia)
Amaranthaceous weeds:
redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus)
Cruciferous (brassicaceous) weeds:
wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis), shepherdpurse (Capsella bursa-pastoris)
Leguminous (fabaceous) weeds:
hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens), common vetch (Vicia sativa)
Malvaceous weeds:
velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)
Violaceous weeds:
field pansy (Viola arvensis), wild pansy (Viola tricolor)
Rubiaceous weeds:
catchweed bedstraw (cleavers) (Galium aparine)
Convolvulaceous weeds:
ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted momingglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)
Labiate weeds:
purple deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)
Solanaceous weeds:
jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)
Geraniaceae weeds:
Carolina geranium (Geranium carolinianum)
Scrophulariaceous weeds:
birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronica hederaefolia)
Composite weeds:
common cocklebur (Xanthium strumarium), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisia princeps), tall goldenrod (Solidago altissima)
Boraginaceous weeds:
forget-me-not (Myosotis arvensis)
Asclepiadaceous weeds:
common milkweed (Asclepias syriaca)
Euphorbiaceous weeds:
sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)
Graminaceous weeds:
barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare)
Commelinaceous weeds:
Asiatic dayflower (Commelina communis)
Equisetaceous weeds:
field horsetail (Equisetum arvense)
Cyperaceous weeds:
rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)
Furthermore, the present composition also has herbicidal activity in flooding treatment of paddy fields against various weeds such as listed below.
Graminaceous weeds:
barnyardgrass (Echinochloa oryzoides)
Scrophulariaceous weeds:
common false pimpernel (Lindernia procumbens)
Lythraceae weeds:
Indian toothcup (Rotala indica), redstem (Ammannia multiflora)
Elatinaceae weeds:
waterwort (Elatine triandra)
Cyperaceous weeds:
smallflower umbrella sedge (Cyperus difformis), hardstem bulrush (Scirpus juncoides subsp. hotarui), needle spikerush (Eleocharis acicularis), nutsedge sp. (Cyperus serotinus), water chestnut (Eleocharis kuroguwai)
Pontederiaceae weeds:
Monochoria (Monochoria vaginalis)
Alismataceae weeds:
dwarf arrowhead (Sagittaria pygmaea), arrowhead (Sagittaria trifolia), waterplantain (Alisma canaliculatum)
Potamogetonaceae weeds:
roundleaf pondweed (Potamogeton distincutus)
Umbelliferae weeds:
water dropwort sp. (Oenanthe javanica)
The present composition can also be used to control a wide variety of weeds which are growing or will grow in non-cultivated lands such as a levee, riverbed, roadside, railroad, green field area of a park, ground, parking area, airport, industrial place (ex. factory, storage equipment), fallow field, idle land of an urban area; wood lot, grasslands, lawns, forests, and the like. The present composition also has herbicidal activity against various aquatic weeds, such as water hyacinth (Eichhornia crassipes), which are growing or will grow at rivers, canals, waterways reservoirs and the like.
In the present composition, the mixing ratio of the insecticidal organophosphorus compound to the present imide compound, it may vary within a range which the herbicidal activity of the present imide compound can be increased, is usually 0.1:1 to 10000:1, preferably 1:1 to 500:1, more preferably 1:1 to 100:1, much more preferably 2:1 to 25:1 by weight.
The present composition may be usually used in the form of formulations such as emulsifiable concentrates, wettable powders, flowables, granules and the like which can be prepared by mixing with solid carriers, liquid carriers, and the like, and if necessary, adding surfactants, other adjuvants and the like.
In such a formulation, the present imide compound and the insecticidal organophosphorus compound are usually contained at the total amount of 10 to 80% by weight.
The solid carrier to be used in the formulation may include, for example, the following materials in fine powder or granule form: clays (e.g., kaolinite, diatomaceous earth, synthetic hydrated silicon oxide, Fubasami clay, bentonite, acid clay); talc and other inorganic minerals (e.g., sericite, powdered quartz, powdered sulfur, activated carbon, calcium carbonate); and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea). The liquid carrier may include, for example, water; alcohols (e.g., methanol, ethanol); ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone); aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, methylnaphthalene); non-aromatic hydrocarbons (e.g., hexane, cyclohexane, kerosine); esters (e.g., ethyl acetate, butyl acetate); nitrites (e.g., acetonitrile, isobutyronitrile); ethers (e.g., dioxane, diisopropyl ether); acid amides (e.g., dimethylformamide, dimethylacetamide); and halogenated hydrocarbons (e.g., dichloroethane, trichloroethylene).
The surfactant may include, for example, alkylsulfric acid esters; alkylsulfonic acid salts; alkylarylsulfonic acid salts; their polyoxyethylene derivatives; polyethylene glycol ethers; polyhydric alcohol esters; and sugar alcohol derivatives.
The other adjuvants may include, for example, adhesive agents and dispersing agents, such as casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, and synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid); and stabilizers such as PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-/3-tert-butyl-4-methyoxyphenol), vegetable oils, mineral oils, fatty acids, and fatty acid esters.
The present composition can also be prepared by making each of the present imide compound and the insecticidal organophosphorus compound into the above formulations; and then mixing these formulations.
The present composition thus formulated may be applied to weeds or to a place where weeds are growing or will grow as such, or after diluted with water or the like.
Furthermore, the present composition can also be prepared by diluting each formulations of the present imide compound and the insecticidal organophosphorus compound with water or the like; and then mixing these dilutions. Further, the present composition may also be used in admixture or be used together with other herbicides, insecticides, fungicides, plant growth regulators, fertilizers or safener.
The present method is usually carried out by an application of the present composition, as such or after dilution, to weeds or to a place where weeds grow or will grow, and also by application of the present imide compound (or its formulation) and the insecticidal organophosphorus compound (or its formulation) together.
The application amounts of the present imide compound and the insecticidal organophosphorus compound, although they may vary with the mixing ratio of them, weather conditions, formulation types, application times, application methods, application places, and weeds to be controlled, are usually 0.1 to 1000 g for the present imide compound and 0.1 to 10000 g for the insecticidal organophosphorus compound per hectare. In the case of emulsifiable concentrates, wettable powders, flowables, or the like, they are usually applied after diluted in their prescribed amounts with water at a ratio of 100 to 1000 liters per hectare.
The present method can be used, for example, in a corn field, a wheat field, a barley field, a rice field, a sorghum field, a soybean field, a cotton field, a sugar beet field, peanut field, a sunflower field, a rape field, an orchard and a paddy field.